


Hijack Week Winter 2020

by AJaxOfAllTrades



Category: How to Train Your Dragon (Movies), Rise of the Guardians (2012)
Genre: Alternate Universe - Modern Setting, Animal Rescue, Baby Animals, Crossdressing, Cuddling, First Date, Fluff, Hurt/Comfort, Leverage AU, M/M, Nerd!Hiccup, Online Dating, PNAU, Thief!Jack, art show date, dating app, hacker!hiccup, hijack week 2020, league of legends sucks, nervous boys on a date, punk!jack, rum distillery, secret boyfriends, vegetarian jack because why not
Language: English
Status: Completed
Published: 2020-12-15
Updated: 2020-12-21
Packaged: 2021-03-09 21:02:28
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 14,708
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27612491
Author URL: https://archiveofourown.org/users/AJaxOfAllTrades/pseuds/AJaxOfAllTrades
Summary: So...in the interest of rebellion...
Relationships: Hiccup Horrendous Haddock III/Jack Frost (Guardians of Childhood)
Comments: 14
Kudos: 50





	1. Day 1: Cross Dressing

**Summary for the Chapter:**

> Hiccup sees a pretty girl in town.

It was Berk's annual Viking Heritage Festival, and _boy_ did it smell bad. At least, it smelled pretty bad from where Hiccup was, walking past the animal pens on his way to the blacksmith's stall. It probably smelled loads better by the food stalls... Unfortunately, those were placed rather far away from the animals so as not to curb peoples' appetites. Tourism was big around the week of the festival, and it wouldn't stay that way if people could smell the livestock while trying to eat mutton. Mutton, because nevermind the _other_ food stalls, people seemed to think the _only_ thing humans ate in Ye Olde Days was mutton, no matter the era or location, and that's all people tended to buy so they could feel _"authentic"_.

He wasn't totally sure why this festival had become such a big attraction in recent years. When Hiccup was a kid, the festival was mostly for the townsfolk, as a means of celebrating their ancestry. Anyone was welcome, but was a lot less sensationalized back then, and _definitely_ a lot less crowded. He could enjoy it then, without passing by zealots he didn't recognize dressed as Thor or the occasional Confused Girl Dressed In Ren Faire Attire. These people weren't looking for the history and traditions of Hiccup's ancestors. They were looking for a theme party.

There might have also been an aspect to enjoying the festival when he was a kid because his dad wasn't the mayor, so he wasn't pressured to work one of the stalls, and he could just run around with his friends all day. Maybe he was romanticizing the festival out of nostalgia. Whatever. He was still grumpy.

Faint giggling caught his attention and he glanced over at the goat pen it was coming from. There were two beautifully dressed girls, the one with dark skin and short rainbow hair standing on her toes and leaning over the fence, watching with a grin as the one with pale skin and long brown hair kneeled down, reaching in through the fence to pet one of the goats. Both were wearing heavily embroidered dresses, which at first glance looked to be Indian. Probably acquired from the rainbow-haired girl if he was _really_ making snap judgments about people he didn't know...but he couldn't be bothered to lend their clothes much more thought than that. He was too busy watching the pale one, staring at her striking blue eyes and perfect smile as she played with the goat beyond the fence.

His phone buzzed. 

He quickly answered it, hunching his shoulders up on reflex to try and hide the device at his ear as to not ruin any more of the illusion by walking around with modern technology. It did little to nothing to help him. He wasn't exactly taking the traditional dress thing seriously today, having just half-assedly put on a sheepskin vest over a cheap long-sleeved shirt he got from Walmart, much to his father's chagrin. Hiccup had won that battle, since Stoick had been in a hurry, so at least he wasn't walking around in full wool and overheating today. "Uhh...hello?" 

"Where are you, lad?" Gobber, his "uncle" who was running the forge, asked, sounding a little annoyed over the phone. "You were supposed to be here five minutes ago! I can't run the forge without an apprentice, it's too much work for an audience!"

"Ahh... Okay, I'm uh... I'm by the goat pen, I'm on my way," Hiccup said quickly, hanging up and shoving his phone back into his inner vest pocket, nicely out of sight. Hiccup turned his head to give one last look to the pretty girl petting the goat-

Aaaand his heart skipped a beat and anxiety prickled at his spine. The blue-eyed girl had turned to look at him, amusement on her face when he looked back to her, like he'd just confirmed that he had been staring at her before he got the phone call. She smiled at him, and Hiccup swallowed, gave a very awkward hand gesture that may have been a wave, may have been his way of trying to _wave off her gaze_ , and he hurried along towards the blacksmith's stall.

* * *

A few hours of working in the forge found Hiccup sweating and miserable. Don't get him wrong, he actually _loves_ working the blacksmith's stall. In fact, he had his own (more modern) forge in his dad's garage that he used in his free time. But this, what he was doing now, wasn't a display of craftsmanship as much as it was a display of process, and Hiccup found himself wishing he'd just worn the damn historically accurate Viking outfit instead of this polyester nightmare.

_'Dad was right. Figures.'_

He glanced out at the people who stopped by to watch them work, hand up to his forehead to wipe away sweat, when he caught a glance of beautiful blue eyes staring _right at him_. 

Damn, he definitely had a weakness for blue eyes...but Astrid's couldn't hold a candle to this girl's, no way. 

She and her friend were tucked close to each other, watching the show...or at least, the shorter one (wow, she was _astoundingly_ short) was. The taller one, the blue-eyed girl with the perfect smile, was watching _him_. They were talking, quietly, and Hiccup couldn't hear them from where he was, but he was _sure_ he knew what the girl had said to her friend after a moment of watching. He wasn't _great_ at reading lips, but what he saw combined with her expression as she turned her head towards her friend _but never once took her eyes off him_ was...

_'He's cute.'_

Hiccup blushed darkly, and thankfully Gobber seemed to realize he was distracted. One hand came down on his shoulder and turned him towards the forge again. "You know better than to get distracted doing this kind of work, Hiccup," Gobber scolded, before turning back to his own work. Hiccup, grateful for the nudge back into reality, got back to work. He cast another glance out to the girl, only a brief one...

He was met with a cocky smirk and a mischievous twinkle in her eyes that he previously thought was unique to Heather...whenever she flirted with Astrid.

_Fuck._

He looked back to his work quickly, hoping his red face could be written off as working in the hot forge, trying to distract himself from the mysterious girl. 

* * *

"Thanks for letting me borrow this dress, Tooth."

Toothiana and her best friend, Jack, had settled at a picnic table in the park. The two of them had heard about the Viking Heritage Festival from a friend in their sister city, Berk, and decided to make a day of traveling from Burgess to see it. Jack had managed to find a vendor selling bowls of barley stew that smelled _really_ good, but Tooth had not had a lot of faith in the vegetarian options like her friend had, and ended up bringing _her_ lunch with her from home. 

She looked up from her food at Jack, who had tied his long, brown wig back with a ribbon to keep it from getting in his food. She still wasn't sure _how_ he got his wigs to look so natural... "Oh, I'm sure you're enjoying it," Tooth teased him, rolling her eyes with a little smile. "That guy you said you saw looking at you? You love the attention."

"That's totally true," Jack laughed. "But it's also just really pretty. And twirly and swishy and fun to move in."

"Figures you'd like playing with it. If you like it so much, maybe I should just _give_ it to you."

Jack blinked at that and grinned, rubbing the back of his neck a little. "Nah, c'mon, your family sent this to you from India, didn't they?" 

Tooth smiled softly and nodded. "Yes, but they send me so many clothes, and that dress looks wonderful on you. Just keep it! I have plenty of them that would look _terrible_ on you."

"Wh-? _H_ _ey!"_

Tooth burst into laughter and shook her head, picking at her food again. "Just hurry up and eat, Jack. There's still some stuff we haven't seen, and I think the blacksmiths are doing a demonstration in the forge right now. I'd love to watch it!"

Jack nodded and chuckled, finishing off his food so they could throw out their trash and head back into the active areas of the festival. Sure enough, there was a crowd at the lit forge, so Jack and Tooth headed over to see if they could see what was happening. Almost immediately upon reaching the stall, though, Jack nudged her in the shoulder and pointed to a somewhat disgruntled looking skinny guy working the forge. "That's him!" he whispered, grinning. "That's the guy who was staring at me." 

Tooth chuckled and looked the guy up and down, but her gaze was drawn back to the actual work being done, the shaping of red hot metal being far more interesting than a skinny white guy to her. But before she could actually say anything, Jack was leaning in towards her again. "He's cute," he whispered, making her chuckle a little. Then, another giggle from Jack. "He looked over here again."  
  
Tooth tore her eyes away from the blacksmith's work in time to see Jack crack his signature crooked grin. She glanced at the boy in the stall, who was now pressing his lips together and _bright red_ , and it definitely didn't look like it was from the heat of the forge. She giggled along with him. "Why don't you approach him?" she asked, smirking herself.  
  
That made Jack turn red and look away. "Tooth, c'mon, he's probably straight, he's staring at me like this because he totally thinks I'm a girl."  
  
Tooth rolled her eyes and grabbed his arm, giving him a shake. "People can like both, y'know," she pointed out. "Why not talk to him when he's done in there and find out for yourself? It's not like you have anything to lose here, Jack. We're just visiting. If it goes wrong, you won't have to see him again."

Jack pursed his lips and sighed, nodding. "Yeah, I guess you're right... He looks like he's gonna be a while though...if you still think it's a good idea after we've walked around for a bit, I'll talk to him...but only if you come with me, okay?"  
  
Tooth grinned and nodded, already moving to tug him away. There were more things to see at the festival, after all, and Tooth knew if Jack spent the next hour staring at the blacksmith boy, he would spook himself and not go through with it.

* * *

Another hour of work, and the demonstration was over, and Gobber could go back to just doing his thing on his own. Hiccup was more than happy to get out of the forge, and fully intended on running home, either to change his shirt into at _least_ the linen tunic his father suggested he wear (because there was no way he was going full wool outer layers right now), or just...sit shirtless in front of a fan to try and dry the sweat. Maybe shower. He didn't smell great. Either way, he was _way too hot_ right now, and just felt gross.

However...as he was exiting the back of the forge, he was met with two silk-clad girls. The rainbow-haired girl had her hands on her hips, smiling and looking at her much paler friend expectantly... But she was looking down, fidgeting a little. Up close, Hiccup could see that the taller of the two was actually a bit shorter than him, which wasn't apparent from far away given how short her friend was in comparison.

She looked nervous. Why did she look nervous? An hour ago, this girl was giving him the flirtiest look he'd ever seen and carrying unbelievable confidence.

"Uhhh...hi," Hiccup finally said, after staring at the two for a moment.

"Hi!" The shorter girl said, looking at him now. "My friend noticed you staring, so we wanted to come and talk to you."

A rock settled in Hiccup's gut at that. " _OH_. Well, that. Uh. That is... Gee, I was uh. Your dresses are so... _embroidered_ _!_ Eye-catching, yeah, I was uh, is that... Where did you get those? That's what I was wondering. Yep. I didn't mean to be staring at _you,_ I was just really curious about the-"

"I'm a guy." 

The deep voice was just as shocking as the words. She - _he,_ rather - was blushing pretty darkly now and rubbing the back of his neck, looking at him from behind the hair swooping down in front of his face. "Uh...?" was all Hiccup could manage for a moment.

"I'm a guy. Cross-dressing. You were staring...I-I just... Thought you should know that? Because if you're not into that kind of thing, you'd probably want to know. So you don't go on thinking I'm a girl...so you don't keep staring i-if you're not into guys, y'know?"

Gods, that was almost precious. In anonymity, this guy had cockily gone around knowing just how good he looked, but... So did Hiccup read him right? Did this guy think he was cute? Was he nervous because he thought Hiccup might not be into him now? 

Wow, that was an interesting change of pace.

"I'm bi."

Blue eyes looked up to him in surprise, and then a little smile grew on his face. " _Oh_." 

"See, I _told_ you," the girl said, nudging the pretty boy in the side. "Now if you'll excuse me, I'm gonna go look at some of the little shops and leave you two to it. Call me if you need me~," she sang, before slipping past her friend and heading off in the direction of the vendor stalls.

The boy stammered for a minute, watching her go, before looking back at Hiccup, momentarily stunned. Nervous.

Hiccup was sure that stunned, nervous expression was mirrored on his own face. "So uh..."

The boy blinked at him, before taking a deep breath, seeming to steel himself before standing up a little straighter and smiling again. Apparently, he was just trying to shake off his nerves. It must have worked, because the next moment, he was stepping a little closer and leaning in to smile up at Hiccup, taking advantage of that whole 'I'm adorable in this dress and I know it' vibe. "So... What's your name~?"

Oh gods. "It's uh... It's Hiccup." He waited for the inevitable 'is that a nickname?', but it didn't come. He was only met with another surprised expression, but it was replaced with a little smile. "Y-yours?"

A grin now, perfect teeth, confidence returned, twinkle in his eye. "I'm Jack."


	2. Day 2: PNAU/RPNAU/First Time but it's actually Cuddle Time

**Summary for the Chapter:**

> Sometimes you just need a big hug and a good cry.

"Hiccuuuuuuup!" Jack whined, draping himself over his boyfriend's shoulders and nuzzling his cheek. "Are you done yet?"

Hiccup looked up from his project and turned his head to look at Jack, chuckling a bit. He was quite used to Jack whining at him when he wanted something and thought nothing of it at first. "Why, did you need something?"

"Cuddles."

Hiccup scoffed and rolled his eyes, leaning in to peck Jack on the cheek. He looked back down at the mechanism he was working on - parts, really, for a bigger project later. He and Tadashi were teaming up on some _secret_ project...or, rather, Tadashi asked him for a favor, and Hiccup wasn't allowed to see it until it was done, "in case it goes horribly," Tadashi had said. He remembered some of the Baymax tests where his friend almost got the shit beat out of him by a malfunctioning nursebot, so he conceded to Tadashi's wishes and let him keep it a secret to save face. "I'll be done soon, don't worry," he said.

Behind him, Jack groaned and slumped against his back. Thankfully he was seated in a sturdy wooden chair...if this was his desk chair, they'd be sprawled out on the floor by now with how much Jack was clinging and dragging. "How long?" He was still whining, but there was _something_ Hiccup picked up on that time that had him turning his head again. Getting a closer look at Jack, he saw the red rimming his eyes and the faint redness of his nose and cheeks...swollen lips... _oh no_.

The project could wait, he decided, and delicately put it down in its protective case. "About right now," Hiccup said, standing up and turning to catch Jack around the waist. Hiccup knew well enough that Jack's childish whining right now was a cover for whatever had him crying earlier...and he'd deny it if Hiccup asked, or pointed it out. "C'mon, let's go to bed. I definitely need a break." He leaned in to give Jack a little kiss on the neck as he pulled him away from the desk.

Jack followed him easily, mouth curling up into a grateful smile as Hiccup tugged him into the bed. He wasted no time in wrapping his arms around Jack, just holding him close. "Like this?" Hiccup asked, not pushing too much in case Jack wanted a different position.

Jack seemed perfectly content though. He nodded, kissing HIccup's jaw before settling down to rest his head against Hiccup's chest. Hiccup pulled the blanket up over both of them, to Jack's shoulders, and moved one hand up and down Jack's back. The other gently brushed into his hair, pushing it back so Hiccup could reach to press a kiss to his forehead. He felt Jack's fingers curl into his shirt, and the anxious bouncing of his heel as his boyfriend tried to calm down. Jack took a slow, shuddering breath in...

And then the flood gates opened. 

It was a little quiet sob at first, but then when Jack inhaled again, it came out as almost desperate crying. Jack turned his head to hide his face in Hiccup's shirt as he shook, and faintly the brunet felt rather than heard a "noooo" against his chest, Jack clearly not being at all happy with this second wind of tears.

Hiccup responded by leaning down to bury his nose into Jack's hair, continuing to just gently rub his back. "It's alright," he whispered. "It's okay, Jack... I'm right here, it's alright..."

Hiccup held him like that until the crying subsided, and then he let up his hold on the back of his head. Jack immediately turned his head to the side to suck in a greedy, shaky breath before letting it out sharply. Then, he laid his head back down again, not seeming to care that he was pressing his ear and hair into Hiccup's now very wet shirt. Hiccup didn't comment on it. He wanted Jack to feel safe in his arms, not called out for crying. He just kept Jack there, securely against him, warm under the blankets. Jack's erratic breathing eventually slowed, his sharp shaky breaths becoming few and far between as he started to calm down.

Finally, one slow inhale, and long exhale, and Jack's shoulders lost their tension as he melted against his boyfriend. "M'sorry," he said quietly, voice cracking a little. 

"It's alright," Hiccup said again, kissing his head once more. "Don't apologize, Jack..." He smoothed Jack's hair down a little, watching with a bit of amusement as it popped back up into its natural spiky state once his hand had passed. "You're okay."  
  
Jack didn't respond. He just kept his head where it was, his breathing slowing down little by little until it was completely relaxed. He knew Jack was still awake by the feeling of his fingers toying with the fabric of his shirt, and Hiccup just let him do what he wanted in comfortable silence, never once loosening his grip. Whatever had his boyfriend so upset, he could tell Jack didn't want to talk about it, he just wanted to be held, and Hiccup wasn't going to let him go any time soon. 

It took some time, since Hiccup wasn't tired and Jack was actively fighting it, but they ended up falling asleep like that, in each other's arms.


	3. Day 3: Royalty/Threesome Thursday but it's actually First Time and not smut

**Summary for the Chapter:**

> There's a first time for everything.

**Notes for the Chapter:**

> "Who brings home a box of abandoned kittens?" -Faith

"Jack, I need you to bring home kitten food."

Jack sort of stared into space with the phone at his ear as he listened to Hiccup's odd request. Hiccup sounded a little panicked, a little out of breath, and there was _something_ happening in the background that made Jack a little suspicious. _Something_ being _tiny squeaky meows_. It took him a moment to respond, mouth moving but no words coming out, before finally, "Hic...? Why? What's up?"

"I'll explain when you get home, okay? I gotta go, my mom's calling me."

And then he hung up.

Jack was confused. If Hiccup had brought home a kitten, he could have just said so? Jack wouldn't have been upset, there was no need for explanations. Still, he shook his head and headed for the pet store. It was only a little bit out of his way, so he didn't mind much, and bought the brand that Hiccup had requested over text. Lots of soft food... Jack was starting to wonder how many kittens Hiccup must have brought home to warrant this much.

He got a few more texts from Hiccup, requesting baby shampoo, which wasn't really a problem...but then _a new small litterbox?_ This was going a little too far. Jack was walking home from work. He couldn't just pile all this into a car and drive home, no. So he texted back that he could only carry small things and started making his way home. Surely they had a cardboard box they could just put some cat litter into as a temporary fix, right?

Jack was beginning to understand just what Hiccup had done when he got home and spotted Valka's car in their driveway. Hiccup didn't associate with his mother much. She had kind of walked away from him and his dad, disappearing without a trace, and only came back into their lives when Hiccup was 20. His dad had easily accepted her back, but Hiccup had a harder time forgiving her. He didn't talk to her as much as it seemed Valka would like - in fact, he really only talked to her when she reached out to him, or when he visited his dad - but Valka was a _vet_.

He wasn't surprised at all to come in and see Hiccup and Valka on the floor with a box of kittens in their living room. Toothless was sitting next to the box, trying to peer in, but when he noticed Jack, he immediately turned and headed for him, rubbing up against his legs. Hiccup had clearly not been petting Toothless enough because of the kittens he and his mom were caring for. It was hard to tell if the black cat was jealous or just needy as usual.

Careful not to accidentally whack Toothless with the bag from the pet store swinging from his wrist, he leaned down to scoop up the spoiled rotten cat into his arms and kicked off his shoes, heading over to where the box of kittens was. Once he got a good look inside, he gasped slightly. 

They looked hungry and dirty, but none of them looked injured, at least. Valka was gently feeling at their legs one at a time to check them, but for the most part, the little kittens were crawling all over each other and meowing and squeaking. They were _so small._ Jack couldn't imagine why someone would abandon a box of them somewhere, which is what he presumed must have happened given Hiccup's urgency over the whole thing.

"I brought the food and shampoo," Jack said softly to not startle the babies, kneeling down next to Hiccup and balancing Toothless with one arm. He handed his fiance the bag. "Where did you get them?"

"Uhhh..." Hiccup looked up at Jack, troubled. "I found the box outside the shop in the back. Someone just left them there, and I didn't want to just dump them on the animal hospital when my mom's a vet, y'know?"

"And it's a good thing you called me first, Hiccup," Valka said, gently picking up one of the kittens and taking the shampoo out of the bag. "Thankfully none of them are hurt, but they need a good washing. I'll take them one at a time. One of you get a little litterbox set up for the dears and the other get to feeding them." She walked away towards the bathroom, probably to wash it in the sink.  
  
"I'll go dig out a box," Jack said, putting a hand on Hiccup's shoulder and setting Toothless down. "Should we get a new box for them to be in, too? That one's a little dirty and beat up."  
  
Hiccup nodded, so Jack stood up, but a sniffle made him pause. He looked back to his fiance to see him wiping his face with his sleeve.

"H-Hic?" he asked, crouching back down again. Hiccup looked over at him, and Jack gasped to see tears in Hiccup's eyes. Jack had never seen that before...he'd never seen Hiccup cry. Hiccup wasn't sensitive to criticism, at least not outwardly. He wasn't a cryer. He didn't even cry when Jack had proposed to him. Seeing tears in his sarcastic, dry, emotionally balanced (mostly) fiance shook Jack. "Hey..." he breathed, putting a hand on Hiccup's back. "Hiccup..."

"Fuck...sorry," Hiccup mumbled, reaching to wipe his eyes again. He was being careful not to touch his face with his _hands_ , but it meant wiping his own tears away was pretty ineffective. "I-I don't... This is stupid, I just... These poor kittens, they _barely_ have their teeth, they're lucky they don't have fleas, they're practically starving...someone could have taken them to a _shelter_ or something, b-but they just _left_ them there behind the shop? Some-somewhere so dangerous where they'd only be found on accident?"

Jack let out a little breath, listening to Hiccup's words before pulling him into a hug. He supposed it made sense...the first time he ever sees Hiccup cry, and it's because someone left a box of kittens for dead behind the auto shop. 

"Yeah, but you rescued them, Hic," he whispered. "They're okay, they're not hurt. We're gonna take care of them, get them ready to be adopted, and find them homes, alright?" Jack promised him, nuzzling his cheek a bit and smiling. "They're going to be just fine."

Hiccup nodded a little into Jack's shoulder. "Ugh..."

Jack couldn't help but chuckle at the noise of disgust Hiccup had made. "Not used to crying?" he asked.

Hiccup nodded again and sniffed. "I hate it..."

Jack grinned. "Y'know something? This is the first time I've ever seen you cry...and I'm kinda glad."

That seemed to confuse Hiccup, because the brunet pulled back, red eyes, puffy face, pout on his lips. "Huh?"

"I'm- _no,_ Hic, I'm not happy you're _crying_ , it's that the first time I'm seeing you cry is because of your...your compassion and empathy for defenseless creatures. It's...fitting." He reached up to touch Hiccup's cheek, wiping away some of the tears there since Hiccup couldn't touch his own face after handling the dirty kittens. "I love you."

Hiccup let out a surprised laugh at that and shook his head, moving to lean into Jack again. "Oh gods... Well, that's _sappy_... I love you, too."

**Notes for the Chapter:**

> This one was a daily hijack prompt from the Official Hijack Discord. You can find the link to join the server on the hijack-week tumblr page!
> 
> Also thanks Toffyy for the idea of Valka being a vet and helping them with the kittens.


	4. Day 4: Cuddle Time/Secret Lovers but it's actually PNAU/RPNAU and League of Legends is a terrible game that nobody likes

**Summary for the Chapter:**

> Video games and rivalries...

**Notes for the Chapter:**

> Because apparently nothing inspires me to write more than an opportunity to needlessly shit on League of Legends for four paragraphs, completely unrelated to the prompt.

This was entirely Snotlout's fault. Only _he_ could rope them all into playing such a bad excuse for a game like League of Legends. Jack couldn't figure out how he managed it. Snot had managed to round up some of his own friend group, and some of Jack's, to play together. Jack, Hiccup, Snotlout, Caleb, and Tuffnut were all sitting in Hiccup's bedroom with their laptops, furiously mashing mouse buttons and outright shouting at each other. Claude and Ruffnut had long since stopped making fun of them, and were instead complaining about being bored while their twins ignored them.

Well, actually no, Jack could tell _exactly_ how he'd gotten them all here. Jack and Snotlout hated each other, and Snotlout had played that angle to convince him. All he had to do was say something about his lack of courage and skill, make a few shots at his pride, and Jack had agreed (rather shamefully) to play, just to prove him wrong. Hiccup and Snotlout were cousins, and Hiccup was a soft-spoken kind of guy. Nerdy, skinny, awkwardly tall, easy to push around. Snotlout tended to walk all over Hiccup, and had probably twisted his arm (literally) to get him to agree to host all of them in his bedroom, instead of on something like Discord. Or maybe Hiccup just didn't want to add Snotlout as a friend on any social platform, and it was easier for his peace of mind to just allow them to cluster in his bedroom if it meant his online sanctuary was safe. Jack wouldn't blame him if that were the case... Ruffnut and Tuffnut, twins who grew up with Hiccup, were absolutely chaotic and probably agreed immediately. The same went for the _other_ set of twins, Caleb and Claude - friends of Jack who were also pretty chaotic in their own right. 

The rest of their friends had opted out of this. They were the smart ones. They escaped this miserable fate... Because here's the thing about League: it's not a _terrible_ game. Jack would concede that the gameplay was really good, actually. What made it terrible was the community of players - everyone was an _asshole_. The majority of League players were _so shitty_ , there was a stereotype about them that only sad gamer fuckboys without friends or lives play the game _._ That wasn't true. The reason every player was an absolute _dick_ was because of _what the game did to you_. Whether you were a casual player just picking whatever character was free to play that week, or someone who had spent hours on perfecting build sets for each beloved Champion in their roster, by the midway point of any match, you turn into a jerk. The game pits you against another team of five, sure...but in a way, it pits you against your own teammates as well.

Five minutes into the game and Hiccup had already let the first bottom tower fall, and Jack was barely holding off the middle lane. Tuffnut and Caleb were just kind of frantically going where they thought they were needed, because most of them had never played before and no one knew what they were doing. Snotlout was tanking top, and doing a fine job on his own, but he was _screaming_ at everyone else for doing so badly. Tuffnut, who _never_ lost his temper, finally snapped at Snotlout to _shut the fuck up_ , and the two had been arguing about it ever since. Caleb and Hiccup were the only ones who had mostly kept their cool - even Jack had taken to cussing out Snot and Tuff for fighting... _at the top of his lungs_. He was a pacifist, but this stupid game had him wanting to beat the absolute shit out of Snotlout.

Graciously, by _some_ miracle, their team won, and Snotlout cheered like he hadn't been antagonizing everyone in the room for 45 minutes. "Alright guys, let's queue up for anot-"

 **_SLAM_ **

Snotlout's laptop had been shut almost on his hands, Hiccup standing over him with a scowl on his face, glaring down over his glasses at his cousin. "We're _not_ playing that again. It's turning everyone toxic. We're going to play Mario Kart. It's lighthearted and not as disastrously competitive. I am _not_ listening to more of your screaming in my house!"

Jack could only watch as the two glared at each other. His tongue jutted out to start fiddling with the ring in his lip as the atmosphere in the room grew much more intense and a little more awkward. Caleb had withdrawn with his laptop and moved to sit next to Claude on the bed. Tuffnut was "oooooooh"-ing from behind Jack, eyes glued on the pair. Even Ruffnut, Jack could see out of the corner of his eye, was leaning in like her brother, eager to see what was going to happen.

Hiccup didn't often stand against anyone. He preferred to mostly keep his head down and tended to be absorbed into the whims of his much more aggressive friends...and Snotlout, who terrorized Hiccup any chance he got. For something to really set Hiccup off, it had to be so chaotic it jeopardized his otherwise peaceful reality. Now, after suffering through that nightmare of a match, Hiccup's jaw was set, his green eyes focused hard as he stood tall over Snotlout.

Finally, Snotlout rolled his eyes and gathered his backpack, putting his laptop away. Jack couldn't help but smirk, impressed, but not _that_ surprised, that Hiccup had won the battle of wills. "Mario Kart's _lame,"_ Snotlout scoffed, standing up. "I'm going home where I can play with people who don't _suck_."

"See you later, Snot-head!" Ruff called after him, smirking as Tuff snickered. But then she turned to Hiccup. "But we're gonna head home, too. This one-" She threw an arm over her twin's shoulders. "-needs to chill out. At home." 

Hiccup's shoulders finally relaxed once Snotlout was out of the room, and he sighed a bit. "Guess that means you don't wanna stay and play Mario Kart after all, huh?" he asked.

"I'll stay," Jack said, standing up from where he sat on the floor and stretching. "And I'll wipe the floor with your ass, Haddock."

"Ohhhh no," Claude said, standing up too. "We're not sticking around if you two are gonna do this again. You can't do anything without arguing with each other!"

Their friend groups had merged because Hiccup and Jamie were good friends. They had met in some of their college classes. For the most part, everyone else got along pretty well... Aside from Jack and Snotlout, of course, and it was easy to figure out why - Snotlout was obnoxious and most of the group didn't like him. He purposely antagonized Jack, just like he did everyone else.

But Hiccup was no Snotlout. He was generally quiet, a little awkward, and really kind, if a little sarcastic. His constant sassy quips at Jack shouldn't have been much of an issue, since he made them with everyone, but they sure seemed to rub Jack the wrong way. He always snapped back with snark of his own. Lately, they'd taken every chance they could get to compete with each other, and it was pretty tiresome to experience from the outside. After a while, everyone else just started leaving them to it. They weren't too worried about Hiccup. Sure, he was almost painfully nerdy sometimes, and Jack looked like the kind of guy who would beat Hiccup up, but it would never come to that. Jack wasn't a bully, and he was actually _really gentle._ Some of his friends would even say _soft_. Plus, Monty and Jamie were exceptionally nerdy themselves, and they were two of Jack's closest friends.

Everyone just figured they were two clashing personalities. Caleb and Claude weren't about to stick around to watch them get absorbed in a competition again.

Jack crossed his arms and pouted. "So you're leaving, too?" he complained. When the twins nodded their confirmation, Jack rolled his eyes. " _Fine_. But I'm not going anywhere. Unless..." He grinned at Hiccup. "Are you scared to race me alone~?"

Hiccup glared at the punk and huffed, muttering something under his breath that sounded like "asshole". "I'm not scared," he said, walking towards the bedroom door. "Because you're not gonna _win_. C'mon guys, I'll walk you out."

Jack snickered and kneeled down on the floor to pack up his laptop while Hiccup walked Caleb, Claude, Ruffnut, and Tuffnut out. When Hiccup came back up the stairs, he stood again. "So, are they gone?" 

Hiccup nodded. "Yeeeep, they're all gone. Left me alone with you. Y-you'd think they would, oh, I dunno, wanna stay and make sure I'm _okay?_ Make sure we don't _kill_ each other or something? But no, they just left. _Gone._ Poof."

Jack couldn't help but laugh and walked over to where Hiccup stood, reaching behind him to shut the bedroom door. "Works for me," he sang, grabbing Hiccup by the front of his shirt and pulling him in for a kiss.

**Notes for the Chapter:**

> To be continued...


	5. Day 5: Dark Hijack/Blowjobs but it's actually Secret Lovers and not smut and they've made a bet on the deductive reasoning skills of all their friends

**Summary for the Chapter:**

> He was a punk, he was a nerd, can they make it any more obvious?

**Notes for the Chapter:**

> Continued from day 4!

The truth was, Hiccup and Jack had instantly had a crush on each other. The first time Jamie introduced them, Jack had thought Hiccup was _adorable_ , from his endless freckles to his endless _snark_ , and Hiccup had thought Jack was witty and fun. But their first meeting had been kind of awkward, and they weren't alone - Hiccup's friend Astrid was there, as well as most of Jamie and Jack's friends. Jack didn't have an opening to flirt, not surrounded by other people. 

Instead, Hiccup's snark had somewhat put him at odds with Jack, or at least it seemed like it. Jack would say something, and Hiccup, without even thinking about it, would say something sassy in response. Sometimes directly at him, sometimes in passing. It usually resulted in Jack shooting back, and so began their little quips at each other whenever they would hang out. Their friends seemed to think they weren't getting along, but Jack was having fun, and he could tell Hiccup was, too. They just let their friends think they had developed a little rivalry.

Eventually came the opportunity for Jack and Hiccup to hang out outside of their friend circle. It was purely on accident, too. There was this used vintage music, book, and game store in the indie shop district. Over the summer, Jack had wandered in to look at some records, and Hiccup had come in a few minutes later looking to sell his old books. It was a nice surprise that they ran into each other, and Jack immediately jumped on the opportunity to start flirting. They'd spent a couple of hours in the store before migrating to a local coffee shop, and then they'd headed to Hiccup's house. They hadn't _done_ anything, but they'd gotten along well and flirted like crazy, and finally they were able to make plans to meet up again.

That was six months ago. They'd been officially dating for four months now, hiding it behind petty competitions that usually helped get the two alone together...like right now.

Now that all their friends were gone, the boys were _all too happy_ to unwind from that disaster of a game. They hadn't even bothered to put the Mario Kart disc into the console and _pretend_ they were going to play. Instead, Hiccup had pressed Jack down against the bed and they were making out. Jack's arms were draped over his boyfriend's shoulders, one hand threading affectionately through Hiccup's hair as they kissed. When Hiccup broke away from his lips and started trailing kisses down Jack's neck, his breath hitched and he tightened his grip. "Hic..."

His neck was sensitive, but Hiccup never obliged him any time he did this, even though Jack always tipped his head back and arched into the feeling, wanting Hiccup to bite him, to leave a mark, do anything more than the gentle kisses that drove him insane. But leaving marks on Jack would make their relationship obvious to their friends. And...why were they hiding it, again? "Mm... _Hic_ _,_ please," he begged, trying to press Hiccup's face a little more insistently into him.

Hiccup pulled back a little, panting a bit, a little smile on his face. "You know if I do that, everyone's gonna know we're a thing, remember?" His voice was teasing. He knew how _needy_ Jack got when they were together, and Jack knew full well that Hiccup loved it. 

Jack blushed. "I don't see a problem with that."

A pause. "You don't?"

Jack blinked, and looked up at Hiccup, surprised. "Well...no. Did you think I did?"

Hiccup looked just as surprised. Slowly he sat up, straddling on of Jack's legs. "Yeah, I mean, I kinda did? I thought you wouldn't want anyone to know about us 'cause you're so... _you_ , and I'm so _not_ , so I said we could keep it a secret."

Jack sat up with him, scooting closer and wrapping his arms around him again. _"First of all,_ I like that you're so _you_. Second...I thought _you_ wanted to keep it a secret so your friends wouldn't give you shit." He smiled at Hiccup and pecked his lips lightly, chuckling a bit. "I just went along with you."

Hiccup laughed awkwardly, looking down, leaning in to press his forehead into Jack's shoulder. Jack couldn't help but smile at how endearing it was. He knew his boyfriend was blushing now. Hiccup's voice was a little muffled, but still easy to hear, when he spoke. "So...how are we gonna tell everyone we've been lying to them for four months?"

Jack laughed at that, turning to kiss the side of Hiccup's head. "Fuck," he whispered with a little giggle. "You're right, that's gonna be painful and weird."

"So can we just keep it a secret then?"

Jack huffed and pressed his face into Hiccup's hair, grinning a bit. He was about to agree, maybe they should just let their friends find out on their own, when an idea struck him.

"How about we play a little game instead?"

"It always scares me when you say tha-ah!" Hiccup pulled away to pout when Jack pinched his ass.

"C'mon, 80% of my ideas are _actually_ fun and you enjoy them."

" _Fine, fine._ " Hiccup rolled his eyes. "Tell me your idea."

"What if we make a little bet?" Jack's eyes twinkled as he spoke. "We don't tell them, but we pretend to be _really_ bad at hiding it, and we wait for someone to say something."

Hiccup snorted. "I think you have a little too much faith in their intelligence, babe. Have you _met_ my friends?"

"I bet if we make it really obvious, someone'll say something in...two months." Jack all but ignored Hiccup's words, instead grinning at him.

Hiccup smirked. "Y'know what? Fine. I'll take that. And if no one says anything after two months, you make good on your bet in front of everyone."

"Ten dollars?" It was low, barely a bet, but they weren't doing this for the gamble. They didn't want high stakes.

"You're on."

Jack giggled and shuffled a little closer to Hiccup. He tilted his head to the side, opening up his neck again. "Okay, good...can we continue, then~?"

Hiccup scoffed a bit, but he grabbed Jack's hips and pushed his punk boyfriend back into the bed, earning a happy moan as he finally bit his throat, sucking to bring up a nice dark mark on Jack's pale skin.

* * *

The next day found Jack thoroughly ravished, and very happy with the sight of himself in the mirror. Hickeys littered his neck and he blushed at his reflection. Hiccup had really gone crazy on him, and it was about damn time. It was too bad that he still wasn't allowed to throw himself at his boyfriend in public, but he consoled himself knowing that the moment someone said something, Jack could indulge in all the PDA the couple could manage.

On Tuesdays and Thursdays, he had a morning class at 10, and then he'd usually meet up with Hiccup, Jamie, Astrid, and Snotlout before Hiccup and Jamie headed off for their noon class together. This time, as he headed over to the bench where the group was huddled together, Snotlout and Jamie were clearly shocked to see Jack - or rather, seeing the state he was in. The reaction had him blushing all over again and he tried not to grin _too_ wide. "Uh, hey?" he said, chuckling a bit.   
  
"What the hell happened to you?" Snotlout demanded, gesturing to Jack's neck.

"Someone have a fun night?" Jamie teased, smirking a bit.

Jack scoffed and pretended to be embarrassed about it, putting a hand over the marks on his neck. "Yeah, well, after Snot's stupid fucking game yesterday, I needed to blow off some steam," he said as he kicked at Snotlout's shin. He missed on purpose. He didn't actually want to hurt the idiot...well, he wasn't _going_ to, anyway. He _did_ want to.

"Who's the unlucky bastard?" Snot shot back, kicking back at Jack _hard_. He wasn't courteous enough to miss.

Jack jumped back, cussing under his breath. He scowled at Snotlout. "Fuck off, douchebag," he spat, walking over to Jamie and putting his friend between him and Hiccup's jerk cousin. "How about instead of worrying about _my_ love life, you focus on your own? Oh, wait, I forgot, you don't have one. _No one fucking likes you_."

"The fuck did you say?!" Snotlout stood up, ready to tear through Jamie to get to Jack, but Hiccup grabbed one arm while Astrid grabbed the other. 

"Aaaalright, nope, you're not doing this!" Hiccup said, surprisingly strong enough to hold Snot back on his side, though of course Astrid was doing more than half the muscle work on hers. "Walk away, no fighting, we don't need to see you two beat each other up!"

Snotlout grunted, struggling for a minute before he jerked back and stormed off. Jack flipped him off behind his back. Jamie spun around and grabbed Jack's wrist, shoving it down and hissing at him to stop.

"Jamie, c'mon," Hiccup said, shrugging one shoulder and nodding his head in the direction of their building. "Let's just go now, grab a snack or something before class starts, okay?" 

Jamie glanced at Jack, who grinned sheepishly, and sighed, shaking his head. He released Jack's wrist and grabbed his backpack. "Alright, Hic. See ya, Jack. Bye, Astrid."

"Bye," Astrid said, hands on her hips, glaring at Jack as the two boys walked away. When they were out of earshot, she walked over and punched Jack on the arm. "The hell is wrong with you? Why do you _always_ antagonize Snotlout like that?" 

"Ow!" Jack flinched and put a hand on the spot she'd hit, scowling. "Come on, Astrid, he's a dick, you know it. He needs someone to take him down a peg. Besides, he started it!"

"You didn't have to respond," she scolded. "He's not worth the effort. Come on, let's go to the cafe and get you some of that gross peppermint tea or whatever that you like so much, so you aren't so stressed before your next class."

Jack rolled his eyes but nodded, shoving his hands in his pockets and following her. "Don't judge me for my drink choices," he mumbled, a little indignantly.

The topic of his... _lover_ didn't come up again. Day one, down.

* * *

The next time their 'secret' came up, it was a week later, and this time it was Hiccup covered in bruises. Somehow Jack had been _much_ more aggressive than Hiccup had. Hiccup had been a dazed, blushing mess by the time Jack was done, and Jack _loved_ it, seeing his boyfriend like that. He couldn't even stop looking at Hiccup as he, Hiccup, and a good chunk of their friends were all hanging out in Jamie's living room. Eventually, and probably to get Jack to stop staring at him, Hiccup had suggested that he wanted cookies, and everyone had immediately sent Jack off to the kitchen to make them. 

While Jack was in the kitchen, Jamie grinned at Hiccup, waggling his eyebrows. "Looks like someone had a good time, eh, Hic?" he teased.

Fishlegs, who had been pointedly _not_ looking at Hiccup, blushed at Jamie's suggestive tone and scoffed. "I-it's none of our business," he said, clearly uncomfortable.

Ruffnut, since she _loved_ teasing Fishlegs, leaned over the large boy and in towards Hiccup. "Someone's been macking all over our little Hickey! Get it? _Hickey?"_ And then she started making gross kissing noises. 

Hiccup groaned, pulling his shirt collar up to try and hide the bruises, turning red himself. "Shut up, guys, Fish's right, it's _none of your business."_

Jack put the cookies in the oven and came out, grinning mischievously. "Are we making fun of Hiccup?" he asked, leaning over the back of the couch Jamie was sitting on. "And how he looks like he got in a fight with an octopus and _lost?"_

"You're one to talk," Jamie laughed, glancing to the side at his friend. "Last week you looked just as bad after you slept with your _mystery man._ "

"When are the cookies gonna be done?" Fishlegs quickly changed the subject, causing Ruffnut and Tuffnut to laugh and nudge him on either side.

Jack laughed too, and the conversation moved on. He glanced at Hiccup, who looked _smug_ that no one had said anything about _them_ yet, the jerk.

* * *

Two months came and went quickly. Jack and Hiccup weren't exactly subtle, stealing glances at each other, showing up absolutely ravished and messy after people _knew_ they'd been left alone together...there were even strong flirty undertones to their bickering! And yet, two months after their bet, to Jack's dismay, no one had once suggested they were together. And, as they'd agreed (and rehearsed), the next time the whole lot of them were together, Hiccup turned to Jack with a grin.

"It's been two months, Jack. Pay up."

There were a few questioning looks as Jack rolled his eyes, dug the $10 out of his wallet he'd put in there the day before, and handed it over to his boyfriend. "Fine, whatever, you win," he grumbled, trying to hide his smile.

"Okay, what the hell?" That was Pippa, looking between the two. "What's been two months?"

Hiccup laughed and rubbed the back of his neck, pocketing the money. "Okay, well uh, two months ago, Jack and I made a little bet."

Jack blushed and looked down, finally grinning. "I bet that someone would say something in two months, about..." He trailed off.

Hiccup finished making the point by reaching over and taking Jack's hand, giving it a squeeze. He scooted over to sit next to Jack, giving him a kiss on the cheek. "I figured even if we made it obvious that we were together, none of you would figure it out."

"So...you've been dating, and keeping your relationship a secret because of a _bet?_ To _test us?"_ Astrid asked, crossing her arms and looking at them hard.

Jack shrank a little into Hiccup, laughing nervously. Hiccup looked just a little nervous, too. "Uh..." Jack swallowed. "...Yes?"

" _Nooooo....._ " That was Jamie. When Jack gave him a weird, slightly offended look, the brunet rolled his eyes and dug out his own wallet. Jack watched with his mouth agape as his best friend pulled out a $20 and handed it over to Astrid.

Astrid smirked and pocketed the twenty. "I _told_ you it was something _dumb_ , Bennett," she sang. "Six months they've been screwing, and they hid it for a _bet_."

Shock. Indignant huffing. Many questions. Teasing. But, no hard feelings when was said and done.

And Jack was, despite losing out on his bet, happily able to cuddle up to his boyfriend while they hung out with all their friends, so did he really lose, after all?

**Notes for the Chapter:**

> Thank you, Snowflakeofberk, for helping me wrap this one up! I was totally stuck.


	6. Day 6: First Date/Kinks but it's actually Crime Boss/Mafia/Criminal and there's no special reason it's being posted on the wrong day except I just didn't feel like doing it right

"Okay, Jack, if you turn left at the next split, you should end up over his office in about fifty feet," Hiccup said through the earpiece. Jack reached up and tapped once to let him know he'd heard him, otherwise not moving. The night guard was directly beneath him in the hallway, and there was no way Jack could move without him hearing. Hiccup already knew the guard was there, watching the security cameras from their van a few blocks away. "There's no one else on the floor but him, so you should be good to keep moving once he clears the hall. Hang in there, okay?" 

Jack responded with another single light tap. Once meant yes, two meant no, three meant _help._ They'd come up with that system early on in their partnership.

Jack could barely see out of the vent grate, but he thought he saw movement...away from him? A moment later, Hiccup spoke up again. "Alright, he's down the hall. He's got headphones in, so move slowly and you'll be fine." 

One last tap, and Jack started moving again. He was agile, light, _small_ , and quiet, but not quiet _enough_ that he'd risk crawling in the ceiling with someone close by. Air vents weren't as sturdy as the movies made them out to be, or as roomy. Or safe, for that matter. He could easily fall through the ceiling if he moved wrong, or be cooked alive if the HVAC turned on while he was up there. Thankfully it was a decent temperature outside. Plus, with all the dust and anything else that Jack could very much confirm was coating the inside of these vents, he could end up with lung issues _real quick_. He was careful, though. He moved slowly, kept his head down, and wore a filtered mask over his mouth and nose (because it's always a good idea to wear your mask _over your fucking nose)_.

As Hiccup guided him, he turned left at the split in the ducts and carefully made his way down. Fifty feet? Should be the second vent. 

Sure enough, just as he'd reached it, Hiccup spoke up in his ear again. "Alright, you're over his office. There's motion sensors in the room, but you're too high up to trigger them, and there's no cameras. I'm not picking up on any recording devices. Just give me a minute to disable the sensors and you can unscrew the vent..." Jack tapped once. He could hear Hiccup doing his thing, mumbling to himself... "Okay, you're good. And the guard just went into the elevator, heading down. Land lightly. He's only one floor below." Another tap.

Jack carefully reached behind him and unzipped the pouch resting on his back, fastened to his belt. He eased out a small screwdriver and zipped the pouch back before getting to work on the vent grate. Keeping in mind the guard on the floor below him, he kept his other hand hooked into it to keep it from clattering to the floor as he unscrewed it. One unusual noise, especially a loud one like that, could bring the guard right back up here, and Jack would be in big trouble. Once he'd gotten it loose, he pulled it up into the duct out of the way and eased himself out of the new opening in the ceiling, landing quietly on the plush carpet of the office.

Almost immediately, Hiccup was speaking to him again. "Alright, you're alone on the floor. Nothing's recording. Walk me through what you see. If there's a safe in the office, it's not digital. I can't find a signal. You're on your own cracking it."

It was a relief to be able to speak, even if his voice was muffled through the mask he wore. "I'm facing the window. Heavy L-shaped desk right in front of it. Half-height filing cabinet to my left, next to the bookshelf. Also heavy, ornate. To the right- _ugh..._ fancy bar cart. Looks like expensive _everything_ in there... Isn't this an office building? Does he day-drink in here? Is that a thing when you're rich?"

"Jack, complain later. We're on a job. Keep going. What else do you see?"

"Another bookshelf, matching the one on the other side. I'm already there, Hic. What do you take me for?"

"You found the safe?"

"Duh. It's in the bottom cabinet of the bookshelf on the right side of the room. Close to the bar cart. All his personal effects are on this side of the room." Jack kneeled down in front of the safe, looking it over. "Hey Hic, I have good news for you."

"Oh no."

"This is one tough safe to crack. About the best our guy can get without going digital. Guess what my specialty is."

"Gee, Jack. I don't know. It's not like we've been working together for years and I don't know how insufferably confident you are about your burglary skills. Do tell, what's your specialty? Explosives? You don't have a lot of time before the guard comes ba-" _Click._ "-ck...you just got it open, didn't you?"

"What am I looking for?" Jack sang a little, grinning.

Hiccup sighed. "The client said the hard copy's about an inch thick. There'll be an eagle watermark on the back of each page." 

That was easy. "Found it. You know he probably has a copy on a drive somewhere, too," Jack pointed out as he slipped the bundle of papers, clasped together securely with a binder clip, into the bag he'd brought with him. He got to work re-locking the safe. "He'll be ready with lawyers as soon as he notices."

"Our client is ready _now_ ," Hiccup reminded him. "All of them are. Now come on, I'm waiting for yo- Jack. Get back into the ceiling _now_. The guard's back in the elevator, coming back up. He's ahead of schedule."

 _Shit._ Jack tapped his ear as he shut the cabinet and swiftly made his way back to the hole in the ceiling. It was just as hard getting back in as it was getting out, and Hiccup was talking to him the whole time, which wasn't helping his nerves. "He's out of the elevator, and heading your way. Are the lights off in the office?" Jack didn't tap yet. He was screwing the grate back into place and needed both hands. He was in a hurry, and had no way of knowing if he was dropping dust and paint chips on the ground. He just had to hope he wasn't...or if he was, the guard didn't notice.

"Jack, can you hear me? He's heading down the hall towards the office. I don't know what tipped him off. He's ten feet away."

Jack popped the screwdriver into his mouth, which was not easy with his mask, leaving him needing to bite down on the handle with his teeth just to make sure it stayed in his mouth, and tapped once on the earpiece to shut Hiccup up. He eased himself backwards in the air duct until he was at least out of sight of the grate, just as he heard the door to the office open. He couldn't see what was going on, which meant the guard couldn't see him either, but it left Jack at the disadvantage of not knowing what was happening. There were no cameras inside the office.

"Jack, I have no idea if he still has his earbuds in. You should stay still until he leaves again, okay?"

Tap.

"Do you want me to keep talking to you while he's in the room?"

Tap tap.

"Okay. I'll tell you when something changes. Hang tight for now." And then silence. Thankfully, Hiccup hadn't muted himself. He could hear movement, and it was reassuring to know his partner was there and safe. But it was also nice to not have him talking when he really needed to focus. He could hear the strange footsteps moving around the room - what was that guard doing? - and mumbling...but then, he heard the sound of a bottle cap being unscrewed. Jack could guess which direction that sound was coming from.

The night guard was stealing some of the target's expensive booze.

The next thing he heard was the desk chair as the guard sat down, and the sound of a glass being set on a hard wooden surface. Jack stayed absolutely still, positive he hadn't been found, but his blood ran cold when the guard spoke down below. "What do you think you're doing?!"

"Jack, is everything okay?" Hiccup asked. Jack was about to tap out a response and ask for help, but the guard spoke again.

"You mean to tell me you _only_ made me three million dollars this month? You talentless _buffoon! Do_ explain to me _why_ I allow such an imbecile to work in _mine almighty organization?!_ Harumph!" 

Suddenly Jack didn't want to leave any time soon. With a grin, he took the screwdriver out of his mouth and tapped once on the earpiece.

Below, the guard continued. "You want me to move the deadlines from Monday at 12:01 am to _Tuesday_ at 9? _Nine in the morning?_ How dare you! How dare you indeed! It's 11:45 on a Friday night! You have the entire weekend to finish the work! I laugh at you! Hum, humhumhum humhumhum!" The guard had put on a hilariously snobby voice as he talked to himself and enjoyed what was probably the CEO's best scotch. "And what's that nonsense, then? You want your weekend spent in your home to be _paid time?_ Well, it's not _my_ fault you can't finish the work in the ten minutes I have generously given you this evening! Go home! Go home and do your job, you half-witted payroll leech! Humbug! A thousand humbugs to you! You'll finish your work on your own time, and reflect upon your utter incompetence! Humbug!"

"Is he...is he doing Scrooge?" Hiccup asked, clearly having picked up on the guard's little speech down below. Jack, who was grinning so widely his cheeks were starting to hurt, tapped once. With the guard talking so much, he was able to at least get the little tool back into his pouch where it wouldn't clatter in the vent, but it was taking everything in him not to laugh out loud and reveal his position. He was rather enjoying himself, but Hiccup spoke up again. "Jack, the temperature outside is dropping, and the heat's going to kick in soon. You need to get out of the vent." Damn. He would have been out by now if not for this guard. 

Tap tap tap.

"I'm already working on something. You're gonna hear sirens, gunshots, and shattering glass. Don't be alarmed. It's just me."

Well, that was worrying.

It wasn't very long. After a couple of minutes of staying still and worrying that the heat would turn on while he was trapped in a tight steel tube, he heard something. It sounded faint, like it was 10 floors down, but sure enough, gunshots, glass shattering, and sirens. He didn't even want to ask what Hiccup had done. Whatever it was, the guard jumped to his feet. The glass clinked in the mini bar a second later before the guard ran out the door.

And then Hiccup was in his ear once more. "I've disabled the thermostat so the heat won't kick on, but you need to get out of there before it gets cold enough that someone turns it on manually. I'll guide you to the elevator. Go forward, then turn right."

Jack listened, following Hiccup's instructions carefully, doing his best to keep his cool as he slowly made his way through the air ducts. This really was his least favorite method of breaking in, but it was also the least monitored. Finally, he was coming out into the elevator shaft. Hiccup already had it coming to the floor directly below. "It's empty. Hop on now, and I'll have it sent down to the bottom level and stall it there." Once Jack was on, he rode it down to the bottom floor - the parking garage beneath the building. "Okay, I froze the cameras inside and around the elevator. You're good to get out of there."

Jack made quick work of the safety door in the top of the elevator, climbing into the car and securing everything back into place. It was a relief to step out into the parking garage and over the concrete divider in the back. "Are you out?" Hiccup asked, and Jack tapped once. "I'm starting the van. Get here quick." It was a few harrowing minutes before Jack was climbing into the back, and Hiccup drove away. They'd gotten out clean.

* * *

_"The real estate world is shaken after an exposé went live early this morning. An anonymous insider with Pitchiner Development & Construction came forward with building plans, bank statements, and samples of building materials that prove Kozmotis Pitchiner, CEO of the company, was authorizing the use of cheap, unsafe building materials and claiming expenses for materials up to code. This new evidence gives hope to the hundreds of families whose lives and homes were affected by this corrupt practice. People who couldn't afford legal representation after moving into the Pitchiner buildings are now being helped by attorneys-"_

Eret turned to Jack and Hiccup, smiling at them. Jack was pouring himself a shot behind the bar, and Hiccup was seated in the bar stool across from him, watching the TV. Eret spoke up to draw their attention back to him. "You did a wonderful thing for those families," he said. "My law firm didn't have the resources to represent those people without any proof. Pitchiner would have buried us if you hadn't gotten that evidence. But I don't know how I can repay you."

Jack set his glass down and leaned on the bar, shaking his head. "You don't have to worry about it."

Hiccup nodded, touching Eret on the shoulder briefly before swiping Jack's shot glass and tipping it back. He laughed when Jack protested. "He's right. Don't worry about paying us. All that matters is that you and those families have what you need to take him down. We work on an...alternative revenue stream."

**Notes for the Chapter:**

> I guess it kind of became a Leverage AU. I just can't stand to think of my boys as bad guys.
> 
> HUGE thanks to @EavingMal who graciously helped me fix this after I got sick and tired of reading my own writing for a month. This would be a hot mess without them.


	7. Day 7: Crime Boss/Mafia/Criminal/Masturbation Monday except it's First Date and if you noticed the chapter titles are getting longer and more nonsensical you'd be correct and I purposely worked to fill in all 255 characters available for the chapter title

**Summary for the Chapter:**

> Jack's very nervous about his first date with Hiccup.

If you went by his dating profile, Hiccup didn't seem like an easy guy to plan a first date for...especially when you're also _meeting_ him for the very first time. Jack and Hiccup had matched pretty quickly on the app. They'd been chatting and texting for a while, and Jack had thought it was time to actually meet up and go on a date. What he hadn't considered was how _difficult_ it would be to plan such a thing.

Okay, fine. To be completely fair, Jack didn't necessarily need to plan an extravagant date. Ideally, meeting up for coffee and chatting should have been enough. But he knew Hiccup by now well enough to know that he'd be awkward. He knew _himself_ well enough to know _he'd_ be awkward, too. The last thing he wanted was for them to be sitting at a coffee shop table, the only distraction to a lull in the conversation being _getting up to order more coffee_. Not having something to do other than just _sit there_ could end in disaster, even if the worst that would happen is that they would be embarrassed about it later. They knew each other pretty well, after all. One weird date wasn't going to ruin what they had growing between them.

But still...Jack wanted to make their first date fun, special, and as "no pressure" as possible. No pressure on himself or Hiccup to uphold a conversation the whole time, anyway.

He was putting a ton of pressure on himself to organize this.

He was aware of the irony.

A movie was _something_ , but there wasn't anything interesting playing that Jack wanted to see. Plus, his movie tastes didn't totally align with Hiccup's, anyway, so one of them would be a little (or a lot) bored. Dinner was just as bad as coffee, but more expensive, and arguably a little more restrictive. A walk in the park... That was low-profile enough for someone like Hiccup, but Jack wasn't sure if Hiccup would _actually_ be into it, or if he'd find it as charming and romantic as Jack had when Hodgins took Angela to a playground swingset for their first date.

Okay, definitely don't take first date ideas from crime dramas.

Especially not when you've recommended the show a million times over. 

That's just lazy.

Still, that idea stayed in his head as he browsed the internet looking for something to do. It was the closest thing to a good idea he'd had so far. Bar? Terrible idea. Brewery tour? Might be cool, but he didn't think Hiccup was into beer. Art show? Not that Hiccup didn't like art, but that was definitely more Jack's speed. And then he spotted a local news article about an event happening just outside of town, and Jack clicked on it. Oh yes, _yes_ , this was exactly what Jack was looking for. He grabbed his phone and quickly texted Hiccup.

[Jack] Hey, are you free this Saturday?

[Hiccup] Yeah...why?

[Jack] Wanna meet up then? And go on a date with me? Maybe around 6?

It took a little longer for Hiccup to respond to that text, and Jack started to get nervous that he would say no, but after a couple of minutes, he got a response back.

[Hiccup] That sounds good. Where do you wanna meet?

[Jack] Actually...can I pick you up at your place? I wanna take you somewhere cool but I kinda wanted it to be a surprise.

Another long pause. Jack knew that was a little more iffy - you never really know who you're meeting up with online, and inviting someone to your house? Going on a date? Letting them take you somewhere as a surprise? He knew it was a long shot. Hiccup was a smart guy. But then, _finally_ , Hiccup responded.

With an address.

* * *

Jack was nervous. He shouldn't be nervous, and yet he was _extremely nervous_. It was 5:55 and he was sitting in his car in the driveway of the address Hiccup had given him. It looked like a nice house. Hiccup had warned him he lived with his dad, but it should be fine just to knock on the door? So slowly he got out of the car and made his way to the front of the house. 

He knocked and waited.

And the man who opened the door didn't look _anything_ like Hiccup. This man _towered_ over Jack, much like Jack's own father, but where North was jovial and loving, _this_ man was _stern and intimidating_. Jack felt himself shrinking back like a high school boy picking up his date for the prom, being met with a rifle-carrying father protecting his little princess. Actually, he might have felt _less_ unsettled if the man had to depend on a rifle to strike fear into his heart, and not just the steely gaze he was giving him.

"Uhhh...um...hi..." Jack started lamely. "I'm... I'm here to... I'm here to get Hiccup?" His voice cracked. 21 years old, dating experience through the roof, and this strange, large man had set him back before puberty, before any shred of confidence. Fuck. 

"You must be Jack," said the man, frowning. "Come on in. Hiccup's finishing up the dishes. He'll be done in a moment."

How was it that being invited in sounded like a threat? Jack swallowed and took in a deep breath, stepping into the house past the giant. He looked around - the house exterior was nice, but the inside resembled more of a humble cabin. Not that tacky farmhouse decor you get at Karen's favorite craft store, either. There were a lot of antiques, folksy stuff...Viking inspired, mostly. Some things were in impressive shape. Nothing museum-worthy, but still probably worth a lot to collectors, if they were authentic. Desperate to end the agonizing feeling of having holes drilled into his soul by Hiccup's father's hard stare, Jack grasped onto that and ran with it. "Are you...a collector?" he asked, gesturing to a _very_ well-worn axe attached to the wall. 

"Family heirlooms," the man said. Jack suddenly wished he hadn't pointed out the axe. He was afraid the ancient hunk of metal, even as dull as it looked, would be lodged in his skull any moment. The man stepped closer, crowding Jack, and the young man found himself pressing back against the door - when had it closed?! - staring up at him. "Where are you taking my son?" he demanded.

Jack glanced to the room where he could hear Hiccup moving around, water running. Any moment now, Hiccup would turn off the water and come through that hallway, see Jack, and they could go on the date Jack had painstakingly planned. He wanted it to be a surprise, so he nervously looked up at Hiccup's father and took a deep breath. "I...understand why you want to know where I'm taking him, sir... But I want to surprise him."

He was met with a scowl, and Jack got so scared he almost spat out his plans loud enough for Hiccup to hear him...but then Hiccup's father leaned down to his level, and Jack almost switched from _that_ to _begging for his life_. "Then tell me quietly."

_'Oh thank god.'_

* * *

As Jack told Stoick his plans for the evening, Hiccup apparently had to run to his room and change. He had chosen _not_ to wear his date clothes while doing chores. Jack had described the dress code as something between casual and a Sunday brunch. Hiccup hadn't known what to do with that, so Jack had to tell him to just wear a nice dress shirt and jeans and it should be fine. The dress shirt would not stand up well to dishwater.

It was just when Jack was finishing whispering his plan to Hiccup's dad that Hiccup came out from the hallway. Jack abruptly stopped talking, just staring at Hiccup. Stoick took that as his cue to go ahead and leave the boys alone, satisfied with what Jack had told him they were going to do. Once Stoick was out of the room, Hiccup smiled at Jack, awkwardly rubbing the back of his neck, and Jack felt butterflies in his stomach. The photos didn't do Hiccup justice. Even from across the room, Jack could see the freckles on his face, his big, pretty green eyes... Hiccup was thin, tall, much taller than Jack had thought. Taller than him. 

And that awkward smile and wave he gave Jack after a moment of the two young men checking each other out? Yeah, Jack's face was beet red, he could tell from the heat in his cheeks. "Uh... Wow," Jack said, letting out a nervous giggle. "You look great, Hic."

"Oh, uh...thanks," Hiccup said in return, and gods above did Jack like hearing that voice in person instead of over the phone. "You uh...you too." 

Jack grinned, slipping his hands into his pockets as he stood there, still pressed back against the door, before he realized _maybe they should get going_. "Ah, should we... Shall we go?" he asked, stepping away from the door and gesturing vaguely. "A hopefully fun evening awaits."

Hiccup chuckled and nodded, coming over to where Jack stood at the door. Jack's first instinct was to take Hiccup's hand and immediately look away, a bit bashful, but he could see in the corner of his eyes that Hiccup's face went dark red at the gesture, and it made him feel _much_ less anxious about it. Together, they headed out of the house and to Jack's car.

After a few minutes of awkward silence, when their unrehearsed small talk kind of died, Jack realized he definitely should have come up with things to say to fill the car ride. Why was this so difficult? They had great conversations over text! And yet here they were, Hiccup staring out the windshield and Jack wracking his brain to come up with something. _Anything._

"So...where are we going?" Hiccup finally asked, just as Jack was about to say...well, probably something stupid. 

Jack glanced at him for the briefest of moments and smiled a little. "It's kind of a surprise," Jack said. "I wanted to find something to do I think you'd like a lot...but honestly I'm a little nervous about it."

"Honestly? I am too."

"We shouldn't be, right?" Jack asked, letting out a little laugh. "I mean, we talk almost every day, so this shouldn't be so awkward and scary, but..."

"...you're afraid of doing something stupid," Hiccup finished, laughing a little himself. "Yeah. So am I. I'm totally terrified you're going to realize how much of a dork I am after this date's over with."

Jack's shoulders relaxed, glad to know he wasn't the only one scared out of his mind. "I already know how much of a dork you are," he said with a soft smile on his face. "It's one of the reasons I like you so much... We can be dorks together."

"Ah, yeah, I do need to keep in mind how cheesy you are."

Jack was quiet for a long moment, still smiling, before speaking up again. "...We really shouldn't be so worried. It's not gonna be weird unless we make it weird."

"Tell that to my anxiety." Hiccup laughed, only this one was a little freer and a little less awkward.

"Hey, Hiccup's anxiety, shut up," Jack snickered. "I'm trying to sweep him off his feet, here!"

"Well, at least one part of your plan is working~."

"Good... Wait, which part?"

* * *

The rest of the car ride was much less tense after they'd started teasing each other, and soon enough, Jack was pulling into the parking lot of their destination for the evening.

"A...rum distillery?" Hiccup asked, looking skeptically at the series of buildings. The sun was setting by now, so the walkway from the parking lot to the main entrance was mostly lit by string lights. In the distance, he could see garden lights lining a walkway behind the main building. There were a lot of cars...more than Hiccup would think considering it was around 6:30 now. Why would there be so many people?

And then he saw it. A poster advertising a local hot-shot artist. Art shows were more Jack's thing, but this particular artist was a metal worker, and that was something that _really_ intrigued Hiccup. Most of her work was on display around the distillery grounds, which required them to go on a walk. It wasn't a guided tour, so they could enjoy each other's company without hearing a tour guide lead them around and interrupt their date.

Jack really had put a lot of thought into this, huh?

"So...should we go on in?" Jack asked, that nervous tone that had vanished in the car coming back to haunt him.

Hiccup couldn't help but grin. Slowly, he took Jack's hand into his own and gave it a squeeze. "Yeah, c'mon, let's go. I can't wait to see what they've got here."

Jack was grinning wide when Hiccup looked at him, and that brought the butterflies back to his stomach. They were less anxious this time - more excited. Halfway to the entrance, though, Jack spoke up again. "So uh, they do rum samples for tours like this," he said. "You don't have to take one if you don't want to? I'm not gonna. I-I didn't know if rum was your thing, anyway...since we've never really talked about alcohol. I just thought you'd like to see the metal sculptures."

Hiccup squeezed his hand again to calm his date down. "Yeah, rum's not my thing," he confirmed. "Actually, the only time I drink is when my dad's best friend makes mead, as if that's not the most insufferably _old-world_ thing you've ever heard, right?"

Jack laughed, happy they could breeze by the rum tasting with just a wave and shake of their heads. "Hey, if that's what you're into, I'm not judging," he hummed, pulling Hiccup along out the back door of the first building, past the crowd of people lining up for a taste of booze. Jack was driving, but even if he wasn't, he wasn't particularly interested in drinking...especially not on a date. 

Outside, the path wound around from the back porch of the first building. From where they stood just outside the door, Hiccup could see that the pathway wasn't the only thing that was well lit - already, giant metal sculptures were on display in the lawn, lit from above and below. The shadows cast by the sharp angles of the metal pieced together were captivating, and Hiccup found for a moment, he couldn't look away. "Whoa..."

He heard a little amused huff beside him, and felt a hand squeeze his own. Jack shifted their hands until their fingers laced together. "Wow, only a few minutes in and you already like what you see, huh?" he teased, voice playfully flirty as he bumped his shoulder.

"Jack...this is awesome. I had no idea she had a gallery here."

"Her work's only being displayed for a little while longer. We got lucky it was still here this weekend," Jack admitted. 

Hiccup bit his lip, unable to help but smile bashfully at the fact that Jack had really taken so much care in planning a date. It had been a joke, but Jack _was_ right - only a few minutes into this date, and Hiccup was already completely taken by his white-haired companion. "Come on," Hiccup said softly, giving Jack a little tug. "Let's see the rest of it."

As they made their way off the porch and down the walkway, more sculptures came into view, each one lit in such a way that brought the cold metal to life. Hiccup couldn't help but start gushing about the craftsmanship, and soon enough Jack started talking about the lighting, and by the time they reached the center of the distillery, surrounded by buildings, the two of them were engrossed in excited conversation. 

What brought them to a pause was the lack of lighting around what Hiccup assumed was supposed to be a display, but it was too dark out to tell. Without the lights, Hiccup couldn't exactly see what it was. 

Before Hiccup could speak, Jack voiced his thoughts for him. "...Do you think some lights went out?" he asked Hiccup.

"Sorry about this, gentlemen," a voice came from behind them. The boys turned to see a couple of maintenance crew members walking over, lugging an extension cord with them. "Just some problems with the wiring. We'll have the lights back up in about 20 minutes if you wanna sit down, take a break, or come back in a few."

Jack looked over at Hiccup, hand still firmly clasped in his own. Hiccup glanced back at Jack and offered a smile. He could tell Jack was a little nervous about something as small as the lights ruining the mood, so he reassured him. "Well, there's a lot more to see, right? We can come back when the lights are fixed. Wanna go check out the barrel storage?"

Jack's eyes lit up again and he nodded, tugging on Hiccup's hand. "Yeah, that's gotta be cool, right?" 

Together, they made their way to the rows of storage buildings, not once letting go of each others' hands. The first building they went into had a few people there, too, but that didn't deter them from wandering in further and looking around. Barrels were stacked up and suspended all around them, leaving only a narrow walkway and a few narrow staircases for such a wide, long building.

They kept their conversation quiet until the other visitors left, probably to go visit another building. When they were alone, Hiccup spoke up. "This place smells amazing."

 _"Right?"_ Jack said. He'd been looking _everywhere_ , seeming unable to pick a thing to focus on. "I don't really like drinking, but something about the _smell_ of rum and wood is... I dunno, kind of comforting?" It was a hard thing to express.

Hiccup, however, understood. "Yeah, I know what you mean... It's warm. Kinda nostalgic, but I can't really place why." Warm, oak, rum... A dark building, surrounded by crates and barrels, the faint sounds of people enjoying themselves outside, the lights from the windows. It was just a rum storage shed, but somehow it was working out to be one of the most romantic places he'd seen. But maybe that was because of the company.

Said company nodded. "Warm. That's the word..." He was cut off by lights flickering, then suddenly shining brighter outside. "Oh," Jack said, looking at the door. "Do you think that's the one we couldn't see coming back on?" He was already tugging Hiccup along to check.

Hiccup wasn't having any of that. Not yet. "Probably," he said, tugging back on Jack's hand to get him to stop. he reached around him, and took Jack's other hand, forcing him to spin and look him in the eyes. He smiled. "Not yet... I don't wanna leave here, yet." Jack gave him a confused look, so Hiccup decided words weren't the best way of communicating what he was thinking. Instead, he let go of one of Jack's hands, catching his chin and tilting it up. And then he kissed him, soft and sweet. For a moment, Jack was frozen, and Hiccup was worried he'd gone too far, but then Jack's arms slid up over his shoulders and he returned the kiss. 

They stayed there for a minute or so, their kiss not going beyond the gentle, slow pace they'd set. When they broke the kiss to breathe, Jack's face was dark red. Hiccup's was, too. They pressed their foreheads together, just taking the moment to bask in each other.

Finally, they mutually pulled away and headed out of the building, hand in hand.

The mysterious artwork was a giant tree. Hulking metal branches twisted and reached for the sky. The lights surrounding the tree _moved_ , which was why there were issues when they'd first arrived. The shadows danced, creating an illusion of a tree caught in the wind, and they both had to sit down on a bench to just enjoy the show for a while, utterly enchanted.

They stayed a little longer, stopping finally in the distillery gift shop. Jack noticed that some of the artist's smaller pieces were on sale there, and bought one for Hiccup to take home. Hiccup, in turn, bought Jack a little box of rum fudge, because even if Jack didn't drink, that fudge looked absolutely divine...and Hiccup had noticed Jack staring at the display table for a few minutes. 

The drive back to Hiccup's house was much more lively than the drive to the distillery had been, the two of them having so much more to talk about. When they pulled into the driveway, Hiccup didn't want to get out of the car. He wanted to stay with Jack just a little longer...just a little longer.

So he leaned in, gently taking Jack's face in his hands, and kissed him again. Of course, Jack eagerly kissed back.

When they parted, Hiccup grinned and started to get out of the car. "This...was amazing, Jack," he said. "It really was. Thank you for taking me there."

Jack chuckled and reached up, blushing madly and rubbing the back of his neck. "I was hoping you'd say that..."

"Text me when you get home, let me know you got there safe, okay?" Hiccup asked.

Jack nodded, and Hiccup shut the car door, heading inside the house. Jack didn't drive away until the door was closed behind him.

True to his word, when he got home, he texted Hiccup that he made it in one piece, got changed into his pajamas, and flopped into the bed to bask in lingering feelings from the wonderful night he'd had. While he was lying there, his phone buzzed. It was a text.

[Hiccup] Tonight was wonderful. <3

[Jack] Yeah, it definitely was. <3

[Hiccup] It's gonna be a hard night to top, but I think I can do it. Can't wait for our next date. <3 Goodnight, Jack.

Jack covered his face with his hands, grinning wide and taking a moment to just _aaahhhhhhhh-_

[Jack] lakdjf;alghrsaroif

[Jack] Goodnight, Hic. <3

**Notes for the Chapter:**

> In 2017, I went on a tour of the Maker's Mark Distillery to see Chihuly's glass art that's on display on the grounds. The whole time I was there, I couldn't stop thinking about how nice of a date spot it would be, wandering the distillery grounds so late at night with artwork everywhere you turn. No, there was no art being sold in the gift shop.
> 
> This is what I wish my experience had been, instead of going with my family. 
> 
> Yes, the tree lighting situation also happened on my trip. I have some interesting photos of a half-lit "Summer Sun".


End file.
